US20030180435A1 - Separation of carotenoids from fruits and vegetables - Google Patents

Separation of carotenoids from fruits and vegetables Download PDF

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Publication number
US20030180435A1
US20030180435A1 US10/240,583 US24058303A US2003180435A1 US 20030180435 A1 US20030180435 A1 US 20030180435A1 US 24058303 A US24058303 A US 24058303A US 2003180435 A1 US2003180435 A1 US 2003180435A1
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United States
Prior art keywords
oil
lycopene
powder
tomatoes
tomato
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US10/240,583
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English (en)
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John Shi
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Agriculture and Agri Food Canada AAFC
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Agriculture and Agri Food Canada AAFC
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Publication of US20030180435A1 publication Critical patent/US20030180435A1/en
Assigned to HER MAJESTY THE QUEEN IN RIGHT OF CANADA AS REPRESENTED BY THE MINISTER OF AGRICULTURE AND AGRI-FOOD reassignment HER MAJESTY THE QUEEN IN RIGHT OF CANADA AS REPRESENTED BY THE MINISTER OF AGRICULTURE AND AGRI-FOOD ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SHI, JOHN
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the present invention relates to the separation of carotenoids from fruits and vegetables.
  • the present invention relates to a method for the separation of lycopene from tomatoes, lycopene being the principal carotenoid in tomatoes.
  • the method involves supercritical carbon dioxide (CO 2 ) fluid extraction (SFE—CO 2 ) of a mixture of edible oil and fruits and vegetables, and especially to the extraction of a mixture of edible oil and powdered fruits and vegetables.
  • Tomatoes are an important agricultural commodity.
  • the whole tomato is used, for example domestic or restaurant uses of various forms of sliced or diced tomatoes.
  • tomatoes are processed into another product e.g. to form canned tomatoes or ketchup. Many of the latter uses involve removal of the tomato skin from the pulp.
  • Lycopene is the principal carotenoid in tomatoes, typically being in amounts of 85-90% by weight of the carotenoids.
  • Low amounts of other carotenoids e.g. ⁇ -carotene, ⁇ -carotene, ⁇ -carotene, ⁇ -carotene, phytoene, phytofluene, neurosporene and lutein are also present in tomatoes.
  • lycopene is able to function as an antioxidant and it exhibits a physical quenching rate constant with singlet oxygen in vitro.
  • the quenching constant of lycopene was found to be more than double that of ⁇ -carotene and 10 times more than that of ⁇ -tocopherol. Consequently, the potential for and benefits of use of lycopene in a diet is of considerable interest.
  • clinical evidence is being obtained in support of the role of lycopene as an important micronutrient, as it appears to provide protection against a broad range of epithelial cancers. Consumers, researchers and the food industry have dramatically increased their interest in and awareness of the potential health benefits of lycopene obtained from tomatoes. Industrial production of lycopene from tomatoes and other fruits and vegetables is sought by food, nutraceutical and pharmaceutical companies.
  • Lycopene that has been extracted from fresh fruits and vegetables, including tomatoes, or from products of fruits and vegetables has been studied extensively using high pressure liquid chromatography (HPLC) analysis.
  • HPLC high pressure liquid chromatography
  • the usual method of extraction utilizes organic solvents such as chloroform, hexane, acetone, benzene, or carbon disulphide.
  • a lycopene extraction and purification procedure that is capable of being used on an industrial scale and which utilizes an environmentally friendly and chemical-fee procedure, with minimal loss of bioactivity, would be of substantial potential benefit in the food, feed, cosmetic and pharmaceutical industries.
  • High quality lycopene will offer potential benefits to the food industry.
  • a successful commercialization of high-value lycopene production may also improve the competitiveness of nutraceutical products in the global market, and may lead to the use of lycopene in other end-uses.
  • one aspect of the present invention provides a method for the separation of carotenoids from fruits and vegetables, comprising the steps of:
  • the fruit and vegetable is tomato.
  • the mixture separated in step (c) is a mixture comprising the edible oil and lycopene.
  • FIG. 1 is a schematic representation of a flow diagram of the method of the invention.
  • the present invention is directed to the extraction of carotenoids from fruit and vegetable containing the carotenoids.
  • a variety of fruits and vegetables may be used, including mixtures of fruits and/or of vegetables, and a variety of carotenoids may be extracted.
  • a preferred fruit or vegetable is tomato.
  • Lycopene is the principal carotenoid in tomatoes, and the method of the present invention will be described herein with particular reference to extraction of lycopene from tomatoes.
  • the tomatoes used in the method of the invention may be obtained from a variety of sources. Ripe tomatoes are preferred. Un-ripe tomatoes and tomatoes that have matured during storage all tend to contain lower amounts of lycopene, and are less preferred for use in the method of the present invention.
  • the tomatoes may be primarily in the form of tomato skins, as the skin and pericarp layers of the tomato contain approximately 80% of the total amount of lycopene in a ripe tomato. Nonetheless, whole tomatoes and mixtures of tomato skins and tomato pulp may be used. Use of tomato skins, or a composition containing a high percentage of tomato skins is preferred.
  • the tomatoes Prior to being subjected to the method of the invention, the tomatoes need to be converted to a particulate form, referred to herein as a powder form, especially a powder having low moisture content.
  • a moisture content of less than 10% is preferred, especially a moisture content in the range of 6-9% by weight.
  • Higher water contents tend to have adverse effects on absorption of lycopene into the oil, as described herein, and of lycopene dissolution in the mixture of oil and tomatoes. Thus, use of relatively low water contents is believed to be more effective in extraction of lycopene into the oil.
  • the tomatoes are subjected to at least one of mechanical crushing, freezing and thawing, cooking, homogenizing and freezing/dehydration i.e. freeze drying.
  • the tomatoes may be mechanically crushed by any convenient method, including blending the tomatoes into a puree using a high speed homogenizer or bead mill.
  • the tomato puree may be cooked in water or steam.
  • the tomatoes may also be subjected to freeze drying.
  • the tomatoes be subjected to more than one of the above steps, to effect a substantial amount of breakdown of cell walls to permit extraction or release of lycopene.
  • the degree of breakdown of cell walls the higher the potential yield of lycopene.
  • the tomatoes are subjected to a number of steps to form the powder, prior to being subjected to the method of the invention.
  • the tomato skin and pericarp layers may be separated from the pulp of the tomato, which may be accomplished by for example treatment with steam or with lye i.e. sodium hydroxide or potassium hydroxide.
  • the tomato skin and pericarp layers are collected and then mechanically crushed and homogenized into a puree.
  • the puree is treated with an enzyme e.g. cellulase at levels of 200-300 International units (I.U.)/g of solid. This treatment may be carried out at ambient temperature.
  • the puree is then cooked, for example at 60-95° C. for 10-40 minutes, and then freeze dried.
  • the resultant powder is screened e.g. through a screen having a mesh size of 0.004-0.5 mm.
  • tomato material may be used immediately but if stored should be stored in the dark in a cooled and sealed container.
  • the tomato material may be stored in a closed (sealed) container in the dark at ⁇ 18° C..
  • the tomato powder should have a low water content, especially below 10% by weight.
  • the tomato powder especially tomato powder with a low moisture content
  • edible oils may be used, including vegetable and fish oils.
  • the edible oil may be soybean salad oil, canola oil, corn germ oil, olive oil, fish oil or peanut oil.
  • the amount of oil should be 520% by weight of the tomato powder.
  • the ratio of tomato powder to edible oils should be in the range of 95:5 to 80:20, by weight.
  • the mixture of tomatoes and oil is preferably maintained for a period of time e.g. overnight, at ambient temperature in a sealed container that excludes both oxygen and light, prior to extraction.
  • the mixture of tomato powder and edible oil is fed to a supercritical —CO 2 fluid extraction process, also known as SFE—CO 2 .
  • SFE—CO 2 supercritical —CO 2 fluid extraction process
  • Such processes are known.
  • the process operates at temperatures above ambient temperature e.g. at about 45-80° C., and under high pressure e.g. about 350-380 bar.
  • the period of extraction is typically 120-180 min, and recovery of lycopene is typically greater than 55% by weight.
  • the optimum processing parameters e.g. of temperature, time, pressure and oil content, are related to the variety of the tomato and to the quality of the skin powder.
  • the high selectivity of the SFE—CO 2 process under optimum conditions provides a high concentration of lycopene in oil.
  • the method of the present invention is further illustrated by the embodiment shown in FIG. 1.
  • tomato skin and outer pericarp layer 2 are obtained from one or both of fresh tomatoes 3 and fresh tomato skin obtained from the waste of a tomato processing operation 4 .
  • Tomato skin and outer pericarp layer 2 are then cooked, 5 , and subjected to mechanical crushing of the cell wall of the tomato skin, 6 .
  • the resultant puree is subjected to enzyme treatment, 7 , as described herein, and then dried, 8 .
  • the skin powder thus obtained is then conditioned with edible oil 9 to provide conditioned skin powder in the edible oil 10 .
  • the resultant mixture is subjected to supercritical CO 2 fluid extraction 11 to provide lycopene-rich oil 12 .
  • the lycopene-rich oil 12 may be encapsulated to provide a product for sale 13 .
  • the lycopene-rich oil 12 may be subjected to purification steps 14 and sold as pure lycopene 15 .
  • lycopene is an all trans-isomer structure. It is understood to be generally accepted that the all-trans form of lycopene has the highest stability but that the cis-isomers are more bioactive and easier to absorb by human body (high bioavailablity). However, cis-isomers are believed to be stable in the oil medium, and HPLC analysis of extracted lycopene typically shows that the lycopene obtained consists of about 55% trans-isomer and 45% cis-isomer. Thus, the method of the invention is useful to develop a cis-rich lycopene oil medium.
  • the method is also used to develop cis-rich lycopene oil products after trans-isomer lycopene is converted into the cis-form during special pretreatment e.g. by heating the mixture or mechanical blending.
  • the oil also acts as lycopene stabilizing agent.
  • Lycopene is believed to be substantially stable at ambient temperatures, e.g. room temperatures.
  • the product obtained in the method of the invention is dark red in colour, is odourless and is may be used in the form obtained.
  • the mixture of oil and lycopene could be encapsulated for use e.g. as a potential anti-cancer functional food, or for other uses, using existing encapsulating facilities in food and pharmaceutical companies.
  • the SFE—CO 2 process is more environmentally friendly than other processes, especially in that chemical solvents are not used. Thus, steps to remove chemical solvents prior to use of the lycopene in food are not required.
  • the method of the present invention uses a material viz. tomato skins that is generally regarded as a waste material. It provides a product that is useful e.g. in encapsulated or other forms, and has substantial potential as a food supplement and potential as an anti-cancer agent.
  • the skin of tomatoes was separated from the fruit part of the tomatoes by steam peeling.
  • the tomato skin, including the pericarp, was collected, crushed and mechanically homogenized into a puree using a Polytrawn T high-speed homogenizer.
  • the moisture content of tomato puree that was obtained was 88-90% on a wet basis.
  • the tomato puree was subjected to an enzyme-treatment, using 300-units of cellulase/g tomato puree, with stirring at room temperature for 24 hours. Subsequently, the puree was cooked at 70° C. for 20 minutes, and then freeze-dried for 12hr. The moisture content of the product obtained was 9% by weight.
  • the product was ground into a powder, which was screened through a sieve having a mesh size 0.004-0.5 mm.
  • the tomato powder was thoroughly mixed with soybean salad oil, using an oil content of 13% w/w.
  • the mixture of powder and oil was stored in the dark in a sealed container at ⁇ 18° C. until use.
  • Samples of the mixture of powder and oil were subjected to SFE—CO 2 extraction.
  • the extraction was carried out at a temperature of 45° C. and a pressure of 360 bar for 150 min.
  • the product obtained from the SFE—CO2 extraction was a lycopene enriched oil product. Analysis of the product showed that the lycopene consisted of 85% trans-isomer and 15% cis-isomer. The colour was dark red. The product was odourless. The amount of lycopene recovered from the tomato powder was more than 55%, which was comparable to exhaustive extraction with hexane-acetone-ethanol solvent (2:1:1v/v/v).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Fats And Perfumes (AREA)
  • Medicines Containing Plant Substances (AREA)
US10/240,583 2000-04-12 2001-04-06 Separation of carotenoids from fruits and vegetables Abandoned US20030180435A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA002305091A CA2305091C (en) 2000-04-12 2000-04-12 Separation of carotenoids from fruits and vegetables
CA2,305,091 2000-04-12

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US20030180435A1 true US20030180435A1 (en) 2003-09-25

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US (1) US20030180435A1 (de)
AU (1) AU2001250195A1 (de)
CA (1) CA2305091C (de)
DE (1) DE10196043T1 (de)
WO (1) WO2001079355A1 (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040131748A1 (en) * 2002-11-12 2004-07-08 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
ES2241503A1 (es) * 2005-04-19 2005-10-16 Eduardo Sabio Rey Procedimiento para preparar formulaciones enriquecidas en licopeno libres de disolventes organicos, formulaciones obtenidas, composiciones que comprenden dichas formulaciones y uso de las mismas.
US7572468B1 (en) 2004-12-28 2009-08-11 The United States Of America As Represented By The Secretary Of Agriculture Extraction of carotenoids from plant material
US20090304870A1 (en) * 2006-08-02 2009-12-10 Leonardo Rescio Food supplement based on biologicallycopene and process to obtain biological lycopene
US20100055261A1 (en) * 2006-11-07 2010-03-04 Biolyco S.R.L. Process for the extraction of lycopene
KR101081275B1 (ko) * 2004-12-21 2011-11-08 (주)아모레퍼시픽 토마토에서 리코펜을 추출하는 방법 및 그 리코펜을함유하는 항산화용 화장료 조성물
CN102433017A (zh) * 2011-10-27 2012-05-02 王金民 一种焦糖色素的天然替代物制备工艺
US20130085309A1 (en) * 2011-09-30 2013-04-04 John Bean Technologies Corporation Carotenoid extraction from plant material
KR101553642B1 (ko) 2014-06-02 2015-09-16 주식회사 에코마인 토마토에서의 리코핀 수득 방법

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ES2172442B2 (es) * 2000-11-15 2003-12-01 Univ Extremadura Procedimiento para la produccion de un concentrado de licopeno libre de disolventes organicos, concentrado obtenido y composicion que comprende dicho concentrado.
ES2197014B1 (es) * 2002-06-06 2005-03-01 Consejo Sup. Investig. Cientificas Extraccion fraccionada de carotenoides de fuentes naturales con alto contenido en licopeno mediante fluidos supercriticos.
WO2006036125A1 (en) * 2004-09-28 2006-04-06 Gao Shen Sdn Bhd A process for producing lycopene extract
ES2302569B1 (es) * 2005-03-07 2009-06-12 Harinas Y Semolas Del Noroeste, S.A. Procedimiento para la incorporacion de ingredientes y/o aditivos alimentarios en productos de cereales y otros vegetales.
WO2009060482A1 (en) * 2007-11-06 2009-05-14 Pectine Industria S.P.A. Method for extracting carotenoids from vegetable matters
CN102845538A (zh) * 2012-07-03 2013-01-02 江南大学 一种富含顺式构型番茄红素的食用油产品及其制备方法
CN102934702A (zh) * 2012-12-06 2013-02-20 刘道鸣 高效番茄红素食用油产品及制备方法
DE102015111743B4 (de) * 2015-07-20 2019-05-23 Sensient Colors Europe Gmbh Verfahren zur Herstellung von färbenden Zubereitungen unter Verwendung von En-zymen, die färbenden Zubereitungen selbst und Lebensmittel, die diese enthalten
CN105595358A (zh) * 2016-01-14 2016-05-25 青岛农业大学 一种番茄红素的提取方法及应用
CN108452082A (zh) * 2018-05-17 2018-08-28 金华市飞凌生物科技有限公司 一种番茄提取物
KR102125420B1 (ko) * 2018-07-06 2020-06-22 주식회사 에이블 클로로필 함유 추출물의 제조방법
CN113122367B (zh) * 2019-12-31 2024-01-09 丰益(上海)生物技术研发中心有限公司 花生油及其制备方法

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US5932101A (en) * 1996-08-29 1999-08-03 Eastman Chemical Company Process for fluid/dense gas extraction under enhanced solubility conditions
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US1988031A (en) * 1933-09-30 1935-01-15 S M A Corp Method of recovering carotene
US4851339A (en) * 1986-04-01 1989-07-25 Hills Christopher B Extraction of anti-mutagenic pigments from algae and vegetables
US4962275A (en) * 1990-02-21 1990-10-09 United States Of America As Represented By The Secretary Of Commerce Method and apparatus for supercritical fluid extraction solution separation
US5837311A (en) * 1993-12-13 1998-11-17 Makhteshim Chemical Works Ltd. Industrial processing of tomatoes and product thereof
US5789647A (en) * 1994-08-18 1998-08-04 Skw Trostberg Aktiengesellschaft Process for the extraction of natural carotenoid dyes
US5591343A (en) * 1994-09-27 1997-01-07 Nippon Oil Co., Ltd. Process for extraction of carotenoids from bacterial cells
US5897866A (en) * 1996-07-12 1999-04-27 Indena S.P.A. Process for the extraction of lycopene using phospholipid in the extraction medium
US5932101A (en) * 1996-08-29 1999-08-03 Eastman Chemical Company Process for fluid/dense gas extraction under enhanced solubility conditions
US5858700A (en) * 1997-04-03 1999-01-12 Kemin Foods, Lc Process for the isolation and purification of lycopene crystals
US6399105B1 (en) * 1999-01-20 2002-06-04 Peter Donald Collin Sea cucumber carotenoid lipid fraction products and methods of use

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070071861A1 (en) * 2002-11-12 2007-03-29 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
US20040131748A1 (en) * 2002-11-12 2004-07-08 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
US7527820B2 (en) 2002-11-12 2009-05-05 Water Solutions, Inc. Composition resulting from process for extracting carotenoids from fruit and vegetable processing waste
US7138152B2 (en) * 2002-11-12 2006-11-21 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
KR101081275B1 (ko) * 2004-12-21 2011-11-08 (주)아모레퍼시픽 토마토에서 리코펜을 추출하는 방법 및 그 리코펜을함유하는 항산화용 화장료 조성물
US7572468B1 (en) 2004-12-28 2009-08-11 The United States Of America As Represented By The Secretary Of Agriculture Extraction of carotenoids from plant material
ES2241503A1 (es) * 2005-04-19 2005-10-16 Eduardo Sabio Rey Procedimiento para preparar formulaciones enriquecidas en licopeno libres de disolventes organicos, formulaciones obtenidas, composiciones que comprenden dichas formulaciones y uso de las mismas.
JP2008536896A (ja) * 2005-04-19 2008-09-11 レイ エドゥアルド サビオ リコペンに富み有機溶剤を含まない製剤の調製方法、得られる製剤、これらの製剤を含有する組成物、およびこれらの使用
WO2006111591A1 (es) * 2005-04-19 2006-10-26 Eduardo Sabio Rey Procedimiento para preparar formulaciones enriquecidas en licopeno libres de disolventes orgánicos, formulaciones obtenidas, composiciones que comprenden dichas formulaciones y uso de las mismas
US7557146B2 (en) 2005-04-19 2009-07-07 Eduardo Sabio Rey Method of preparing lycopene-enriched formulations that are free of organic solvents, formulations thus obtained, compositions comprising said formulations and use of same
US20080194703A1 (en) * 2005-04-19 2008-08-14 Eduardo Sabio Rey Method of Preparing Lycopene-Enriched Formulations That are Free of Organic Solvents, Formulations Thus Obtained, Compositions Comprising Said Formulations and Use of Same
US8263156B2 (en) * 2006-08-02 2012-09-11 Leonardo Rescio Food supplement based on biologicallycopene and process to obtain biological lycopene
US20090304870A1 (en) * 2006-08-02 2009-12-10 Leonardo Rescio Food supplement based on biologicallycopene and process to obtain biological lycopene
US20100055261A1 (en) * 2006-11-07 2010-03-04 Biolyco S.R.L. Process for the extraction of lycopene
US20130085309A1 (en) * 2011-09-30 2013-04-04 John Bean Technologies Corporation Carotenoid extraction from plant material
US9469843B2 (en) * 2011-09-30 2016-10-18 John Bean Technologies S.P.A. Carotenoid extraction from plant material
CN102433017A (zh) * 2011-10-27 2012-05-02 王金民 一种焦糖色素的天然替代物制备工艺
KR101553642B1 (ko) 2014-06-02 2015-09-16 주식회사 에코마인 토마토에서의 리코핀 수득 방법

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WO2001079355A1 (en) 2001-10-25
CA2305091C (en) 2002-10-22
DE10196043T1 (de) 2003-05-08
AU2001250195A1 (en) 2001-10-30
CA2305091A1 (en) 2001-05-05

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